10H-benzo[G]pteridine-2,4-dione derivatives, method for the production thereof, and use thereof

Abstract

The invention relates to 10H-benzo[g]pteridine-2,4-dione derivatives, to the production thereof, and to the use thereof.

What is claimed is:  
     
       1. A compound having the formula (1): 
       
         
           
           
               
               
           
         
         where I) only 1 R5 or R6 radical is an organic radical having: 
         a) at least two uncharged, protonatable nitrogen atoms not bonded directly to the isoalloxazine ring, or 
         a) at least two positively charged nitrogen atoms not bonded directly to the isoalloxazine ring, 
         and where each of the R1, R2, R3 and R4 radicals is the same or different and is independently hydrogen, hydroxyl, thiol, nitro, carboxylate, aldehyde having 1 to 20 carbon atoms, ketone having 2 to 20 carbon atoms, O-alkyl having 1 to 20 carbon atoms, S-alkyl having 1 to 20 carbon atoms, O-alkenyl having 2 to 20 carbon atoms, S-alkenyl having 2 to 20 carbon atoms, O-aryl having 5 to 20 carbon atoms, S-aryl having 5 to 20 carbon atoms, carboxylic ester having 1 to 20 carbon atoms, carboxamide having 1 to 20 carbon atoms, thioester having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms, and 
         where each of the R5 and R6 radicals which is not an organic radical having a) at least two uncharged, protonatable nitrogen atoms not bonded directly to the isoalloxazine ring, or b) at least two positively charged nitrogen atoms not bonded directly to the isoalloxazine ring, is the same or different and is independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms, or wherein R5 can be acyclic polyol radical selected from the group consisting of arabityl, ribityl, xylityl, erythrityl, threityl, lactityl, mannityl and sorbityl, or an ether, ester or acetal thereof 
         with the proviso that 
         compounds are excluded in which the R1, R4 and R6 radicals are hydrogen, the R2 radical is hydrogen, alkyl having 1 to 8 carbon atoms or cycloalkyl having 3 to 7 carbon atoms, the R3 radical is hydrogen, halogen, alkyl having 1 to 8 carbon atoms, O-alkyl having 1 to 8 carbon atoms or a heterocyclic radical having 4 to 7 carbon atoms, and the R5 radical is an alkyl radical which has 1 to 8 carbon atoms and is substituted by at least by a radical of the formula —N(R 35 )(R 36 ) or a radical of the formula —OR 35 , where the R 35  radical is a radical of the formula —C 1-8  alkyl(amine)-OR 37  or a 7,8-dimethylisoalloxazin-10-yl-C 1-8 alkyl radical and where the R 36  radical is hydrogen or a radical of the formula —C 1-8 alkyl, which may be unsubstituted or substituted, and where the R 37  radical is hydrogen, aryl having 6 to 7 carbon atoms or alkyl which may be unsubstituted or substituted and has 1 to 8 carbon atoms, and 
         additionally excluding compounds in which the R1 and R4 radicals are hydrogen , the R6 radical is hydrogen or a radical having the general formula —C 1-4 alkyl-OC(O)CH 3 , the R2 radical is hydrogen or alkyl having 1 to 8 carbon atoms and the R5 radical is a radical having the general formula —C 1-6 alkyl-N(R 31 )—C 0-3 alkyl-(R 32 ), where R 31  is hydrogen or a radical having the formula —C 1-4 alkyl and where R 32  is a radical having the formula —C 1-4 alkyl-N(R 33 )(R 34 ), a radical having the formula —C 0-4 alkyl-aryl, a radical having the formula —C 0-4  alkylheterocycloalkyl or a radical having the formula —C 0-4 alkylheteroaryl, and where the R 33  and R 34  radicals are each independently hydrogen or -C 1-4 alkyl, and 
         excluding 10-butyl-7,8-dimethyl-3-[2-oxo-2-(1,4,7,10-tetrazacyclododec-1-yl)ethyl]benzo[g]pteridine-2,4-dione and 10-[2-(2-methoxyethoxy)ethyl]-7,8-dimethyl-3-[2-oxo-2-(1,4,7,10-tetrazacyclododec-1-y1)ethyl]benzo[g]pteridine-2,4-dione, or 
         where II) only 1 R5 or R6 radical is an organic radical having: 
         a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and 
         b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, 
         and where each of the R1, R2, R3 and R4 radicals is the same or different and is independently hydrogen, hydroxyl, thiol, nitro, carboxylate, aldehyde having 1 to 20 carbon atoms, ketone having 2 to 20 carbon atoms, O-alkyl having 1 to 20 carbon atoms, S-alkyl having 1 to 20 carbon atoms, O-alkenyl having 2 to 20 carbon atoms, S-alkenyl having 2 to 20 carbon atoms, O-aryl having 5 to 20 carbon atoms, S-aryl having 5 to 20 carbon atoms, carboxylic ester having 1 to 20 carbon atoms, carboxamide having 1 to 20 carbon atoms, thioester having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms, or 
         where each of the R5 and R6 radicals which is not an organic radical having a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, or b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, is the same or different and is independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms or wherein R5 can be acyclic polyol radical selected from the group consisting of arabityl, ribityl, xylityl, erythrityl, threityl, lactityl, mannityl and sorbityl, or an ether, ester or acetal thereof, or 
         where III) R5 and R6 radicals are an organic radical having at least one selected from the group consisting of: 
         a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and 
         b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and 
         where each of the R1, R2, R3 and R4 radicals is the same or different and is independently hydrogen, hydroxyl, thiol, nitro, carboxylate, aldehyde having 1 to 20 carbon atoms, ketone having 2 to 20 carbon atoms, O-alkyl having 1 to 20 carbon atoms, S-alkyl having 1 to 20 carbon atoms, O-alkenyl having 2 to 20 carbon atoms, S-alkenyl having 2 to 20 carbon atoms, O-aryl having 5 to 20 carbon atoms, S-aryl having 5 to 20 carbon atoms, carboxylic ester having 1 to 20 carbon atoms, carboxamide having 1 to 20 carbon atoms, thioester having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms or heteroaryl having 4 to 20 carbon atoms, which does not contain any nitrogen atoms, and 
         and wherein the compound having the formula (20) is excluded: 
       
       
         
           
           
               
               
           
         
         and wherein in variants I), II) and III) of the compound of formula (1), the alkyl radicals and alkenyl radicals may be straight-chain or branched and be either unsubstituted or substituted by at least one radical selected from the group consisting of hydroxyl, sulfanyl, alkyloxy, alkylsulfanyl, alkanoyloxy, amino, alkylamino having 1 to 4 carbon atoms, dialkylamino having 2 to 8 carbon atoms, trialkylammonio having 3 to 12 carbon atoms, and guanidino. 
       
     
     
       2. The compound as claimed in  claim 1 , wherein the organic radical having at least one selected from the group consisting of
 a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and 
 b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, is a radical of the formula (2), (3) or (4): 
 
       
         
           
           
               
               
           
         
         where h is an integer from 1 to 20 and k and 1 are each independently an integer from 0 to 6, and where D and E are each independently hydrogen, halogen, hydroxyl, O—R (VIII)  where R (VIII)  is methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, O—C(═O)—R (IX)  where R(IX) is hydrogen, methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, or thiol and where X is an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom and b) at least one positively charged nitrogen atom, and the aryl radical is a substituted or unsubstituted aromatic system having 5 to 20 carbon atoms or a substituted or unsubstituted heteroaromatic system which does not contain any nitrogen atom and has 4 to 20 carbon atoms, and 
         where the radical having the formula (4) is a heteroaromatic system which is bonded to the isoalloxazine ring via a carbon atom of the heteroaromatic system and which contains at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom and b) at least one positively charged nitrogen atom. 
       
     
     
       3. The compound as claimed in  claim 1 , where the R1 and R4 radicals, which may each independently be the same or different, are hydrogen or methyl, and where 2 of the R2, R3, R5 and R6 radicals are an organic radical of the general formula —(C(D)(E)) h -X or —(C(D)(E)) k -aryl-(C(D)(E)) l -X,
 where X is an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom and b) at least one positively charged nitrogen atom. 
 
     
     
       4. The compound as claimed in any one of  claims 2  or  3 , where X is a radical of the general formula (2): 
       
         
           
           
               
               
           
         
       
       where A is an oxygen or sulfur atom and where n is an integer from 1 to 8 and m is an integer from 0 to 100, and where B is a radical of the formula (3a), (3b), (4a), (4b), (5a) or (5b): 
       
         
           
           
               
               
           
         
       
       and where the R (I)  radical is an aryl radical having 5 to 20 carbon atoms, a heterocyclic radical having 5 to 20 carbon atoms, an alkyl radical, which may be straight-chain or branched, having 1 to 20 carbon atoms, an alkenyl radical, which may be straight-chain or branched, having 2 to 20 carbon atoms, a hydroxyalkyl radical, which may be straight-chain or branched, having 1 to 20 carbon atoms, an ether radical, which may be straight-chain or branched, having 2 to 20 carbon atoms, a thioether radical, which may be straight-chain or branched, having 2 to 20 carbon atoms, or an alkylamino radical, which may be straight-chain or branched, having 1 to 20 carbon atoms, where each of the R (II) , R (III) ,R (V)  and R (VI)  radicals is independently hydrogen, an aryl radical having 5 to 20 carbon atoms, a heterocyclic radical having 5 to 20 carbon atoms, an alkyl radical, which may be straight-chain or branched, having 1 to 20 carbon atoms, an alkenyl radical, which may be straight-chain or branched, having 2 to 20 carbon atoms, a hydroxyalkyl radical, which may be straight-chain or branched, having 1 to 20 carbon atoms, an ether radical, which may be straight-chain or branched, having 2 to 20 carbon atoms, a thioether radical, which may be straight-chain or branched, having 2 to 20 carbon atoms, or an alkylamino radical, which may be straight-chain or branched, having 1 to 20 carbon atoms and where each of the aforementioned aryl radicals, heterocyclic radicals, alkyl radicals, alkenyl radicals, hydroxyalkyl radicals, ether radicals, thioether radicals and alkylamino radicals is substituted at least by one selected from the group consisting of amino radical(s) and alkylamino radical(s), which may be straight-chain or branched, having 1 to 20 carbon atoms,
 and where the radical having the formula (4a) and the radical having the formula (5a): 
 
       
         
           
           
               
               
           
         
       
       is a substituted or unsubstituted heterocyclic radical having 5 to 7 ring atoms including 2 to 4 nitrogen atoms and at least 1 carbon atom and optionally 1 or 2 oxygen or sulfur atoms, where 1 nitrogen atom forms a double bond, and where the radical having the formula (4b) and the radical having the formula (5b): 
       
         
           
           
               
               
           
         
       
       is a substituted or unsubstituted heterocyclic radical having 5 to 7 ring atoms including 2 to 4 nitrogen atoms and at least 1 carbon atom and optionally 1 or 2 oxygen or sulfur atoms. 
     
     
       5. The compound as claimed in  claim 2 , where the organic radical having:
 a) at least two uncharged, protonatable nitrogen atoms not bonded directly to the isoalloxazine ring, or 
 b) at least two positively charged nitrogen atoms not bonded directly to the isoalloxazine ring, is in each case selected from the radicals of the formulae (30a) to (36) 
 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       6. The compound as claimed in  claim 1 , where the 10H-benzo[g]pteridine-2,4-dione derivative of the formula (1) is selected from the group consisting of compounds having the formulae (40) to (49) and (115) to (117): 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         
           
           
               
               
           
         
       
     
     
       7. A pharmaceutical composition comprising at least one compound as claimed in  claim 1  or at least one selected from the group consisting of a pharmacologically acceptable salt, an ester and a complex thereof and at least one pharmacologically acceptable excipient. 
     
     
       8. A coated article, wherein the surface of the article comprises at least one compound as claimed in  claim 1 . 
     
     
       9. A process for preparing a compound of  claim 1 , wherein the process comprises the following steps:
 (A) reducing a substituted nitroaniline of the formula (9) to a substituted o-phenylenediamine of the formula (10) 
 
       
         
           
           
               
               
           
         
         where each of the R7 to R10 radicals is the same or different and is independently hydrogen, halogen, hydroxyl, thiol, nitro, carboxylate, aldehyde having 1 to 20 carbon atoms, ketone having 2 to 20 carbon atoms, O-alkyl having 1 to 20 carbon atoms, S-alkyl having 1 to 20 carbon atoms, O-alkenyl having 2 to 20 carbon atoms, S-alkenyl having 2 to 20 carbon atoms, O-aryl having 5 to 20 carbon atoms, S-aryl having 5 to 20 carbon atoms, carboxylic ester having 1 to 20 carbon atoms, carboxamide having 1 to 20 carbon atoms, thioester having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms, heteroaryl which does not contain any nitrogen atom and has 4 to 20 carbon atoms, —(C(D)(E)) h -OH, —(C(D)(E)) k -aryl-(C(D)(E)) l -OH or an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, 
       
       and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and
 where the R11 radical is hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms, heteroaryl which does not contain any nitrogen atom and has 4 to 20 carbon atoms, —(C(D)(E)) h -OH, —(C(D)(E)) k -aryl-(C(D)(E)) l -OH or an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and 
 (B) condensing the substituted o-phenylenediamine of the formula (10) obtained in step (A) with alloxane or the hydrate thereof to obtain a compound having the formula (11): 
 
       
         
           
           
               
               
           
         
         (C) optionally reacting the compound of the formula (11) obtained in step (B) with an alkylating agent of the general formula T-alkyl, T-alkenyl, T-cycloalkyl, T-cycloalkenyl, T-(C(D)(E)) h -OH, T-(C(D)(E)) k -aryl-(C(D)(E)) l -OH, T-aryl, T-(C(D)(E)) h -X or T-(C(D)(E)) k -aryl-(C(D)(E)) l -X, where the T radical is hydrogen, chlorine, bromine, iodine, p-toluenesulfonyl (OTs), methanesulfonyl (OMs), OH or R 2 S + , where each R may independently be the same or different to obtain a compound having the formula (12): 
       
       
         
           
           
               
               
           
         
         where the R12 radical is hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms, heteroaryl which has 4 to 20 carbon atoms and does not contain any nitrogen atom, —(C(D)(E)) h -OH, —(C(D)(E)) k -aryl-(C(D)(E)) l -OH or an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and 
         (D) optionally reacting the compound of the formula (11) obtained in step (B) or the compound of the formula (12) obtained in step (C) with tosyl chloride, mesyl chloride or iodine, optionally in the presence of a catalyst, and subsequently with an organic compound containing at least one selected from the group consisting of at least one uncharged, protonatable nitrogen atom and b) at least one positively charged nitrogen atom, when at least 1 R7, R8, R9, R10, R11 or R12 radical is —(C(D)(E)) h -OH or 
       
       —(C(D)(E)) k -aryl-(C(D)(E)) l -OH, to obtain the 10H-benzo[g]pteridine-2,4-dione derivative of the formula (1),
 with the proviso that at least 2 R1, R2, R3, R4, R5 or R6 radicals are an organic radical having at least one selected from the group consisting of: 
 a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and 
 b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and 
 
       where each h is an integer from 1 to 20 and k, l are each independently an integer from 0 to 6, where D and E are each independently hydrogen, halogen, hydroxyl, O—R (VIII)  where R (VIII)  is methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, O—C(═O)—R (IX)  where R(IX) is hydrogen, methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, or thiol, and where each X is an organic radical having at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and each aryl is a substituted or unsubstituted aromatic system having 5 to 20 carbon atoms or a substituted or unsubstituted heteroaromatic system which does not contain any nitrogen atom and has 4 to 20 carbon atoms. 
     
     
       10. A process for preparing a compound as claimed in  claim 1 , wherein the process comprises the following steps:
 (A) condensing an amine having the formula R11-NH 2  with a chlorouracil derivative of the formula (13), optionally in the presence of a catalyst to obtain a compound having the formula (14): 
 
       
         
           
           
               
               
           
         
         where each of the R11 and R12 radicals is the same or different and is independently hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms, heteroaryl which does not contain any nitrogen atom and has 4 to 20 carbon atoms, —(C(D)(E)) h -OH, —(C(D)(E)) k -aryl-(C(D)(E)) l -OH or an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, 
         (B) reacting the compound of the formula (14) obtained in step (A) with a nitroso compound of the formula (15) to obtain a compound of the formula (12): 
       
       
         
           
           
               
               
           
         
         where each of the R7 to R10 radicals, which may independently be the same or different, is hydrogen, halogen, hydroxyl, thiol, nitro, carboxylate, aldehyde having 1 to 20 carbon atoms, ketone having 2 to 20 carbon atoms, O-alkyl having 1 to 20 carbon atoms, S-alkyl having 1 to 20 carbon atoms, O-alkenyl having 2 to 20 carbon atoms, S-alkenyl having 2 to 20 carbon atoms, O-aryl having 5 to 20 carbon atoms, S-aryl having 5 to 20 carbon atoms, carboxylic ester having 1 to 20 carbon atoms, carboxamide having 1 to 20 carbon atoms, thioester having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms, heteroaryl which does not contain any nitrogen atom and has 4 to 20 carbon atoms, 
       
       —(C(D)(E)) h -OH, —(C(D)(E)) k -aryl-(C(D)(E)) l -OH or an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and
 (C) optionally reacting the compound of the formula (12) obtained in step (B) with tosyl chloride, mesyl chloride or iodine, optionally in the presence of a catalyst, and subsequently with an organic compound containing at least one tertiary nitrogen atom has been reacted, when at least 1 R7, R8, R9, R10, R11 or R12 radical is —(C(D)(E)) h -OH or —(C(D)(E)) k -aryl-(C(D)(E)) l -OH, to obtain the 10H-benzo[g]pteridine-2,4-dione derivative of the formula (1) 
 with the proviso that at least 2 R1, R2, R3, R4, R5 or R6 radicals are an organic radical having at least one selected from the group consisting of: 
 a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and 
 b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and 
 
       where each h is an integer from 1 to 20 and k, l are each independently an integer from 0 to 6, where D and E are each independently hydrogen, halogen, hydroxyl, O—R (VIII)  where R (VIII)  is methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, O—C(═O)—R (IX)  where R(IX) is hydrogen, methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, thiol, and where each X is an organic radical having at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, antler and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and each aryl is a substituted or unsubstituted aromatic system having 5 to 20 carbon atoms or a substituted or unsubstituted heteroaromatic system which does not contain any nitrogen atom and has 4 to 20 carbon atoms. 
     
     
       11. A process for preparing a compound as claimed in  claim 1 , wherein the process comprises the following steps:
 (A) preparing a substituted aniline having the foirnula (122a) or (122b) by (a) peptide coupling/reduction to an aniline having the formula (121) or (b) reductive amination of an aniline having the formula (121) with aldehydes or (c) Pd-catalyzed coupling of a halide of the formula (124) to an amines of the formula R11-NH 2  or (d) Pd-catalyzed coupling of an amine of the formula (120) to a halide of the formula R11-NH 2    
 
       
         
           
           
               
               
           
         
         
           
           
               
               
           
         
         where each of the R7 to R10 radicals, which may independently be the same or different, is hydrogen, halogen, hydroxyl, thiol, nitro, carboxylate, aldehyde having 1 to 20 carbon atoms, ketone having 2 to 20 carbon atoms, O-alkyl having 1 to 20 carbon atoms, S-alkyl having 1 to 20 carbon atoms, O-alkenyl having 2 to 20 carbon atoms, S-alkenyl having 2 to 20 carbon atoms, O-aryl having 5 to 20 carbon atoms, S-aryl having 5 to 20 carbon atoms, carboxylic ester having 1 to 20 carbon atoms, carboxamide having 1 to 20 carbon atoms, thioester having 1 to 20 carbon atoms, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms, heteroaryl which does not contain any nitrogen atom and has 4 to 20 carbon atoms, —(C(D)(E))h-OH, 
       
       —(C(D)(E))k-aryl-(C(D)(E))l-OH or an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and
 where the R11 radical is hydrogen, alkyl having 1 to 20 carbon atoms, alkenyl having 2 to 20 carbon atoms, cycloalkyl having 3 to 20 carbon atoms, cycloalkenyl having 3 to 20 carbon atoms, aryl having 5 to 20 carbon atoms, heteroaryl which does not contain any nitrogen atom and has 4 to 20 carbon atoms, —(C(D)(E)) h -OH, —(C(D)(E)) k -aryl-(C(D)(E)) l -OH, or an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and 
 where the R20 radical is hydrogen, alkyl having 1 to 19 carbon atoms, alkenyl having 2 to 19 carbon atoms, ether having 1 to 19 carbon atoms, thioether having 1 to 19 carbon atoms, cycloalkyl having 3 to 19 carbon atoms, cycloalkenyl having 3 to 19 carbon atoms, aryl having 5 to 19 carbon atoms, heteroaryl which has 4 to 19 carbon atoms and does not contain any nitrogen atoms, —(C(D)(E)) h-1 -OH, —(C(D)(E)) k-1 -aryl-(C(D)(E)) l-1 -OH or an organic radical containing at least one selected from the group consisting of a) at least one uncharged, protonatable nitrogen atom not bonded directly to the isoalloxazine ring, and b) at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring, and 
 where the Hal radical is fluorine, chlorine, bromine or iodine, 
 (B) reacting the substituted aniline having the formula (122a) obtained in step (A) with violuric acid to obtain a compound of the formula (11z): 
 
       
         
           
           
               
               
           
         
          or 
         reacting the substituted aniline having the formula (122b) obtained in step (A) with violuric acid to obtain a compound of the formula (11): 
       
       
         
           
           
               
               
           
         
         (C) optionally reacting the compound of the formula (11z) obtained in step (B) with tosyl chloride, mesyl chloride or iodine, optionally in the presence of a catalyst, and subsequently with an organic compound containing at least one tertiary nitrogen atom is reacted, when at least 1 R7, R8, R9, R10, R11 or R20 radical is —(C(D)(E)) h -OH or —(C(D)(E)) k -aryl-C(D)(E)) l -OH, to obtain the 10H-benzo[g]pteridine-2,4-dione derivative of the formula (12z): 
       
       
         
           
           
               
               
           
         
       
       where D and E are each independently hydrogen, halogen, hydroxyl, O—R (VIII)  where R (VIII)  is methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, O—C(═O)—R (IX)  where R(IX) is hydrogen, methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, or thiol
 or 
 reacting the compound of the formula (11) obtained in step (B) with tosyl chloride, mesyl chloride or iodine, optionally in the presence of a catalyst, and subsequently with an organic compound containing at least one tertiary nitrogen atom is reacted, when at least 1 R7, R8, R9, R10, R11 or R20 radical is —(C(D)(E)) h -OH or —(C(D)(E)) k -aryl-(C(D)(E)) l -OH, to obtain the 10H-benzo [g]pteridine-2,4-dione derivative of the formula (12): 
 
       
         
           
           
               
               
           
         
       
       where D and E are each independently hydrogen, halogen, hydroxyl, O—R (VIII)  where R (VIII)  is methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, O—C(═O)—R (IX)  where R(IX) is hydrogen, methyl, ethyl, n-propyl, n-butyl, phenyl or benzyl, or thiol and
 with the proviso that 
 I) only 1 R1, R2, R3, R4, R5 or R6 radical is an organic radical having: 
 a) at least two uncharged, protonatable nitrogen atoms not bonded directly to the isoalloxazine ring, or 
 b) at least two positively charged, preferably quaternary, nitrogen atoms not bonded directly to the isoalloxazine ring, or 
 II) only 1 R1, R2, R3, R4, R5 or R6 radical is an organic radical having: 
 a) at least one uncharged, protonatable nitrogen atom(s) not bonded directly to the isoalloxazine ring, and 
 b) at least one, preferably at least two positively charged nitrogen atom(s) not bonded directly to the isoalloxazine ring, 
 or 
 III) at least 2 R1, R2, R3, R4, R5 or R6 radicals are an organic radical having: 
 a) at least one, preferably at least two uncharged, protonatable nitrogen atom(s) not bonded directly to the isoalloxazine ring, and 
 b) at least one positively charged nitrogen atom(s) not bonded directly to the isoalloxazine ring. 
 
     
     
       12. A method for inactivating microorganisms located on or within a subject in need of such inactivation, said method comprising applying upon said subject a compound of  claim 1 . 
     
     
       13. The compound according to  claim 1 , wherein at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring is a quaternary nitrogen atom. 
     
     
       14. The compound according to  claim 2 , wherein said at least one positively charged nitrogen atom not bonded directly to the isoalloxazine ring is a quaternary nitrogen atom. 
     
     
       15. The compound according to  claim 2 , wherein the halogen is selected from the group consisting of chlorine, bromine, iodine and fluorine. 
     
     
       16. The compound according to  claim 2 , wherein D and E are each independently hydrogen or hydroxyl. 
     
     
       17. The compound according to  claim 4 , wherein each of said aryl radicals, heterocyclic radicals, alkyl radicals, alkenyl radicals, hydroxyalkyl radicals, ether radicals, thioether radicals and alkylamino radicals is substituted by one selected from the group consisting of at least two, at least three, at least four and at least five, of said amino radicals andzef alkyl amino radicals. 
     
     
       18. The compound according to  claim 5 , wherein said at least two positively charged nitrogen atoms are quaternary nitrogen atoms. 
     
     
       19. The process according to  claim 9 , wherein each R is selected from the group consisting of methyl, ethyl, propyl and butyl. 
     
     
       20. The process according to  claim 9 , wherein the halogen is selected from the group consisting of chlorine, bromine, iodine and fluorine. 
     
     
       21. The process according to  claim 9 , wherein D and E are each independently hydrogen or hydroxyl. 
     
     
       22. The process according to  claim 10 , wherein the catalyst is a Lewis acid or a Brønsted acid. 
     
     
       23. The process according to  claim 10 , wherein the halogen is selected from the group consisting of chlorine, bromine, iodine and fluorine. 
     
     
       24. The process according to  claim 10 , wherein D and E are each independently hydrogen or hydroxyl. 
     
     
       25. The process according to  claim 11 , wherein the halogen is selected from the group consisting of chlorine, bromine, iodine and fluorine. 
     
     
       26. The process according to  claim 11 , wherein D and E are each independently hydrogen or hydroxyl. 
     
     
       27. The process according to  claim 11 , wherein the positively charged nitrogen atoms not bonded directly to the isoalloxazine ring are quaternary nitrogen atoms. 
     
     
       28. The process according to  claim 11 , wherein one selected from at least two, at least three, at least four and at least five, uncharged protonatable nitrogen atoms are not bonded directly to the isoalloxazine ring. 
     
     
       29. The process according to  claim 11 , wherein one selected from at least two, at least three, at least four and at least five positively charged nitrogen atoms are not bonded directly to the isoalloxazine ring. 
     
     
       30. The method according to  claim 12 , wherein the inactivation of microorganisms is a photodynamic inactivation. 
     
     
       31. The method according to  claim 12 , wherein the microorganisms are selected from the group consisting of viruses, archaea, bacteria, bacterial spores, fungi, fungal spores, protozoa, algae and blood-transmissible parasites. 
     
     
       32. The method according to  claim 12 , wherein said photosensitizer compound is applied upon said subject in at least one selected from the group consisting of the cleaning of teeth, dentures, and dental braces and treatment of a disorder of at least one of dental tissue and of the poridontium. 
     
     
       33. The method according to  claim 12 , wherein said photosensitizer is applied upon said subject for treatment of an infectious skin disease. 
     
     
       34. A method for inactivating microorganisms located on or within an object wherein said method comprising applying to an object during at least one of surface cleaning and coating of said object a compound of  claim 1 . 
     
     
       35. The method according to  claim 34 , wherein the object is selected from the group consisting of medical products, food and drink packaging and hygiene articles.